CH151128A - Process for the preparation of α-isopropyl-B-dimethylaminopropionaldehyde. - Google Patents
Process for the preparation of α-isopropyl-B-dimethylaminopropionaldehyde.Info
- Publication number
- CH151128A CH151128A CH151128DA CH151128A CH 151128 A CH151128 A CH 151128A CH 151128D A CH151128D A CH 151128DA CH 151128 A CH151128 A CH 151128A
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropyl
- dimethylaminopropionaldehyde
- isovaleraldehyde
- formaldehyde
- forms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 α-isopropyl- Chemical group 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910001023 sodium amalgam Inorganic materials 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- DUTFVROVXLHMMG-UHFFFAOYSA-N 2-(dimethylamino)propanal Chemical group O=CC(C)N(C)C DUTFVROVXLHMMG-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von u-Isopropyl-p-dimetliylaininopropionaldehyd. Aldehyde von der allgemeinen Formel
EMI0001.0005
wobei R einen Alkylrest, R' ebenfalls einen.
Alkylrest oder Wasserstoff, R und R' zu- summen: mit der CH-Gruppe auch einen hydroaromatis.ohen Ring bedeuten, sowie Verbindungen, welche solche Aldehyde ab spalten, lassen sich mit Formaldehyd und primären oder sekundären aliphatischen Aminen im Sinne folgender Gleichung leicht zu Aminoaldehyden kondensieren:
EMI0001.0015
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von a-Iso- propyl-ss-dimetliylaminopropional@deIlyd, wel- ehes dadurch gekennzeichnet ist, dass man Isovaleraldehyd mit Formaldehyd und Dime- tllylamin kondensiert. Man kann bei dem Verfahren Isovaleraldehyd und Formaldehyd verwenden, welche aus Verbindungen, die diese Aldehyde abspalten, erzeugt wurden.
Der a-Isopropyl-ss-dimet@ylaminopropion- aldehyd bildet ein wasserhelles, bei 12 mm Druck zwischen 66 und 68 uniersetzt destil lierendes. Cal von stark alkalischer Reaktion. Er löst sich in Wasser fast nicht. Mit Mine ralsäuren bildet er hyb oskopische Salze. Durch Reduktion mit '.\Latriumamalgam er hält man leicht die zugehörige Alkoholbase, welche ein bei 15 mm Druck zwischen 85 und 86 siedendes Öl bildet.
Der a-Isopropyl-ss-dimethylaminopropion- aldehyd soll als Zwischenprodukt für die Herstellung von Arzneimitteln dienen.
<I>Beispiel:</I> 15 Teile Isovaleraldehyd, 21 Teile salz saures Dimethylamin, 25 Teile Formaldehyd- lösung (35%ig) werden: drei Stunden am Rückflusskühler gekocht, bis die Mischung homogen geworden ist. Man schüttelt bei saurer Reaktion mit Äther aus, .versetzt so dann mit Kalilauge im Überschuss' und ge winnt durch Ausschütteln mit Äther ?.0 Teile einer flüssigen Base, den a-Isopropyl-@-dime- thylaminopropionaldeh.yd. Er destilliert als wasserhelles<B>01</B> bei 12 mm Druck zwischen 66 und 68 .
Process for the preparation of u-isopropyl-p-dimethylaminopropionaldehyde. Aldehydes of the general formula
EMI0001.0005
where R is an alkyl radical, R 'also one.
Alkyl radical or hydrogen, R and R 'sum: with the CH group also mean a hydroaromatic ring, as well as compounds which split off such aldehydes can easily be used with formaldehyde and primary or secondary aliphatic amines in the sense of the following equation Condensing amino aldehydes:
EMI0001.0015
The present invention relates to a process for the preparation of α-isopropyl-ss-dimethylaminopropional @ deIlyd, which is characterized in that isovaleraldehyde is condensed with formaldehyde and dimethylamine. In the process, isovaleraldehyde and formaldehyde can be used, which were generated from compounds which split off these aldehydes.
The a-isopropyl-ss-dimet @ ylaminopropionaldehyde forms a water-white, which at 12 mm pressure between 66 and 68 uniierstil lating. Cal of strongly alkaline reaction. It almost does not dissolve in water. With mineral acids it forms hyboscopic salts. By reducing it with sodium amalgam, one can easily obtain the associated alcohol base, which forms an oil that boils between 85 and 86 at a pressure of 15 mm.
The α-isopropyl-ß-dimethylaminopropionaldehyde is intended to be used as an intermediate in the manufacture of pharmaceuticals.
<I> Example: </I> 15 parts of isovaleraldehyde, 21 parts of hydrochloric acid dimethylamine, 25 parts of formaldehyde solution (35%) are: boiled for three hours on the reflux condenser until the mixture has become homogeneous. In the case of an acidic reaction, it is extracted with ether, then treated with excess potassium hydroxide solution and obtained by shaking out with ether? .0 parts of a liquid base, α-isopropyl - @ - dimethylaminopropionaldehyde. It distills as water-white <B> 01 </B> at 12 mm pressure between 66 and 68.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH151128T | 1930-03-20 | ||
| CH147156T | 1930-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH151128A true CH151128A (en) | 1931-11-30 |
Family
ID=25714984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH151128D CH151128A (en) | 1930-03-20 | 1930-03-20 | Process for the preparation of α-isopropyl-B-dimethylaminopropionaldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH151128A (en) |
-
1930
- 1930-03-20 CH CH151128D patent/CH151128A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1545792B2 (en) | Process for the preparation of 4-Hydroxyplperidinen | |
| CH151128A (en) | Process for the preparation of α-isopropyl-B-dimethylaminopropionaldehyde. | |
| CH151135A (en) | Process for the preparation of 1- (piperidinomethyl) -hexahydrobenzaldehyde. | |
| CH151130A (en) | Process for the preparation of a, a-dimethyl-B-methylaminopropionaldehyde. | |
| DE1158083B (en) | Process for the preparation of basic substituted phenylacetonitriles | |
| CH151129A (en) | Process for the preparation of 1- (diethylaminomethyl) -hexahydrobenzaldehyde. | |
| CH235953A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| DE950550C (en) | Process for the preparation of basic substituted phenylcycloalkenylpropanols | |
| CH147156A (en) | Process for the preparation of a, a-dimethyl-B-dimethylamino-propionaldehyde. | |
| DE877457C (en) | Process for the production of amino alcohols | |
| CH151127A (en) | Process for the preparation of a, a-dimethyl-B-diethylaminopropionaldehyde. | |
| AT142910B (en) | Process for the preparation of basic dioxane derivatives. | |
| DE1157607B (en) | Process for the production of locally anesthetically effective amino ethers | |
| DE641865C (en) | Process for the production of condensation products | |
| DE544692C (en) | Process for the preparation of aldehyde bases | |
| AT135705B (en) | Process for the preparation of 6-mono- or 6-dialkyl- or -aralkylamino-2-methylhepten- (2). | |
| CH204726A (en) | Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. | |
| AT257584B (en) | Process for the production of new tetrahydrofuran derivatives | |
| AT214930B (en) | Process for the preparation of new thioxanthene derivatives | |
| DE2047375A1 (en) | ||
| AT233005B (en) | Process for the preparation of a new pyridine derivative | |
| AT124736B (en) | Process for the preparation of 1-phenyl-2-methylaminopropanol- (1). | |
| CH204704A (en) | Process for the preparation of an amino alcohol. | |
| CH151134A (en) | Process for the preparation of α, α-dimethyl-B-piperidinopropionaldehyde. | |
| CH152089A (en) | Process for the preparation of 1-p-oxyphenyl-2-aminopropanol-1. |